Petroleum-based aromatic monomers are widely used to prepare polymeric materials. Such monomers include terephthalic acid, styrene, divinyl benzene, bisphenol A, phenylene diamine, and phthalic anhydride. Since the rigidity and stability of the aromatic ring provides good thermal and mechanical properties, a wide variety of thermoplastic and thermoset materials have utilized these types of monomers
For example, terephthalic acid is a well known commodity monomer that finds widespread use by the plastics industry for the synthesis of films, fibers, and bottles made with polyethylene terephthalate (PET). Other polymers, such as Kevlar, also utilize petroleum-based terephthalic acid or derivatives of terephthalic acid.
The consumption of terephthalic acid, which is often referred to as purified terephthalic acid (PTA), and the corresponding dimethyl ester of PTA are approximately 9 billion lbs per year. (Wittcoff, H. A.; Reuben, B. G.; Plotkin, J. S. Industrial Organic Chemicals; Wiley: Hoboken, N.J., 2004.) The synthesis of PTA is based on petroleum derived para-xylene. The subsequent copolymerization of PTA with ethylene glycol, which is based on petroleum derived ethylene, yields polyethylene terephthalate (PET).
There has been an effort to produce terephthalic acid using biobased technology. One approach involves converting glucose-derived isobutanol to para-xylene from a corn-based platform. Subsequently, the para-xylene is converted to terephthalic acid. Another approach involves preparing terephthalic acid from a biomass containing a terpene or terpenoid, such as limonene. See, e.g., U.S. Patent Publication No. 20100168461.
However, more effective methods for preparing monomers and polymers based on plants or biomass are still desired. In addition, there is a desire to develop processes and products from renewable sources that can substitute or supplement petroleum-based chemicals.